Compound for organic photoelectric device and organic photoelectric device image sensor, and electronic device including the same

Abstract

A compound for an organic photoelectric device is represented by Chemical Formula 1, and an organic photoelectric device, an image sensor and an electronic device include the same.

What is claimed is: 
     
       1. A compound for an organic photoelectric device represented by Chemical Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 1, 
         Ar is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings, 
         X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein each of R a  and R b  are independently one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         each of Ar 1  and Ar 2  are independently one of a substituted or unsubstituted C 6  to C 30  aryl group and a substituted or unsubstituted C 3  to C 30  heteroaryl group, and 
         each of R 1  to R 3  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 30  alkyl group, a substituted or unsubstituted C 6  to C 30  aryl group, a substituted or unsubstituted C 3  to C 30  heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof 
         wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength region of greater than about 530 nm and less than or equal to about 575 nm. 
       
     
     
       2. The compound of  claim 1 , wherein the compound has 4 to 7 aromatic rings. 
     
     
       3. The compound of  claim 1 , wherein at least one of the Ar 1  and Ar 2  groups is one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted phenanthrenyl group. 
     
     
       4. The compound of  claim 1 , wherein in Chemical Formula 1, a cyclic group represented by Ar and bound to a methine group is represented by Chemical Formula 2: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 2, 
         Ar′ is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings, and 
         Z 1  is one of O and CR c R d , wherein each of R c  and R d  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 10  alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c  and R d  is one of a cyano group and a cyano-containing group. 
       
     
     
       5. The compound of  claim 1 , wherein in Chemical Formula 1, a cyclic group represented by Ar and bound to a methine group is a cyclic group represented by one of Chemical Formulae 3-1 to 3-3: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formulae 3-1 to 3-3, 
         Z 1  is one of O and CR c R d , wherein each of R c  and R d  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 10  alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c  and R d  is one of a cyano group and a cyano-containing group, 
         Y 1  is one of N and CR e , wherein R e  is one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         Y 3  is one of O, S, Se, and Te, 
         Y 4  is one of N and NR 18 , 
         Y 5  is one of CR 19  and C═C(R 20 )(CN), 
         each of R 11 , R 12  and R 15  to R 20  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 30  alkyl group, a substituted or unsubstituted C 6  to C 30  aryl group, a substituted or unsubstituted C 4  to C 30  heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group and a combination thereof, 
         m1 is 0 or 1, 
         m2 is an integer ranging from 0 to 4, and 
         n is 0 or 1. 
       
     
     
       6. The compound of  claim 1 , wherein the compound is represented by one of Chemical Formulae 4-1 to 4-3: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formulae 4-1 to 4-3, 
         X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b  wherein each of R a  and R b  are independently one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         Z 1  is one of O and CR c R d  wherein R c  and R d  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 10  alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c  and R d  is one of a cyano group and a cyano-containing group, 
         Y 1  is one of N and CR e  wherein R e  is one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         Y 3  is one of O, S, Se, and Te, 
         Y 4  is one of N and NR 18 , 
         Y 5  is one of CR 19  and C═C(R 20 )(CN), 
         each of R 1  to R 3 , R 11 , R 12  and R 15  to R 20  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 30  alkyl group, a substituted or unsubstituted C 6  to C 30  aryl group, a substituted or unsubstituted C 4  to C 30  heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group and combination thereof, 
         m1 is 0 or 1, 
         m2 is an integer ranging from 0 to 4, 
         n is 0 or 1, 
         each of R 21  to R 23  are independently one of hydrogen, a halogen, a cyano group (—CN), a cyano-containing group, a substituted or unsubstituted C 1  to C 6  alkyl group, a substituted or unsubstituted C 1  to C 6  alkoxy group, and a combination thereof, and 
         p is an integer ranging from 0 to 3, q is an integer ranging from 0 to 4, and r is an integer ranging from 0 to 5. 
       
     
     
       7. The compound of  claim 1 , wherein the compound shows a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 110 nm in a thin film state. 
     
     
       8. The compound of  claim 1 , wherein the compound has a thermal decomposition of greater than or equal to about 280° C. 
     
     
       9. An organic photoelectric device comprising:
 a first electrode and a second electrode facing each other; and 
 an active layer between the first electrode and the second electrode, the active layer including a compound represented by Chemical Formula 1: 
 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 1, 
         Ar is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings, 
         X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein R a  and R b  are independently one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         each of Ar 1  and Ar 2  are independently one of a substituted or unsubstituted C 6  to C 30  aryl group and a substituted or unsubstituted C 3  to C 30  heteroaryl group, and 
         each of R 1  to R 3  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 30  alkyl group, a substituted or unsubstituted C 6  to C 30  aryl group, a substituted or unsubstituted C 3  to C 30  heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof, 
         wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength region of greater than about 530 nm and less than or equal to about 575 nm. 
       
     
     
       10. The organic photoelectric device of  claim 9 , wherein the compound has 4 to 7 aromatic rings. 
     
     
       11. The organic photoelectric device of  claim 9 , wherein at least one of the Ar 1  and Ar 2  groups is one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted phenanthrenyl group. 
     
     
       12. The organic photoelectric device of  claim 9 , wherein in Chemical Formula 1, a cyclic group represented by Ar and bound to a methine group is represented by Chemical Formula 2: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 2, 
         Ar′ is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings, and 
         Z 1  is one of O and CR c R d , wherein each of R c  and R d  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 10  alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c  and R d  is one of a cyano group and a cyano-containing group. 
       
     
     
       13. The organic photoelectric device of  claim 9 , wherein in Chemical Formula 1, a cyclic group represented by Ar and bound to a methine group is a cyclic group represented by one of Chemical Formulae 3-1 to 3-3: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formulae 3-1 to 3-3, 
         Z 1  is one of O and CR c R d , wherein R c  and R d  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 10  alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c  and R d  is one of a cyano group and a cyano-containing group, 
         Y 1  is one of N and CR e , wherein R e  is one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         Y 3  is one of O, S, Se, and Te, 
         Y 4  is one of N and NR 18 , 
         Y 5  is one of CR 19  and C═C(R 20 )(CN), 
         each of R 11 , R 12  and R 15  to R 20  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 30  alkyl group, a substituted or unsubstituted C 6  to C 30  aryl group, a substituted or unsubstituted C 4  to C 30  heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof, 
         m1 is 0 or 1, 
         m2 is an integer ranging from 0 to 4, and 
         n is 0 or 1. 
       
     
     
       14. The organic photoelectric device of  claim 9 , wherein the compound is represented by one of Chemical Formulae 4-1 to 4-3: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formulae 4-1 to 4-3, 
         X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein each of R a  and R b  are independently one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         Z 1  is one of O and CR c R d , wherein each of R c  and R d  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 10  alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c  and R d  is one of a cyano group and a cyano-containing group, 
         Y 1  is one of N and CR e , wherein R e  is one of hydrogen and a substituted or unsubstituted C 1  to C 10  alkyl group, 
         Y 3  is one of O, S, Se, and Te, 
         Y 4  is one of N and NR 18 , 
         Y 5  is one of CR 19  and C═C(R 20 )(CN), 
         each of R 1  to R 3 , R 11 , R 12  and R 15  to R 20  are independently one of hydrogen, a substituted or unsubstituted C 1  to C 30  alkyl group, a substituted or unsubstituted C 6  to C 30  aryl group, a substituted or unsubstituted C 4  to C 30  heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group and combination thereof, 
         m1 is 0 or 1, 
         m2 is an integer ranging from 0 to 4, 
         n is 0 or 1, 
         each of R 21  to R 23  are independently one of hydrogen, a halogen, a cyano group (—CN), a cyano-containing group, a substituted or unsubstituted C 1  to C 6  alkyl group, a substituted or unsubstituted C 1  to C 6  alkoxy group, and a combination thereof, and 
         p is an integer ranging from 0 to 3, q is an integer ranging from 0 to 4, and r is an integer ranging from 0 to 5. 
       
     
     
       15. The organic photoelectric device of  claim 9 , wherein the compound shows a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 110 nm in a thin film state. 
     
     
       16. The organic photoelectric device of  claim 9 , wherein the compound has a thermal decomposition of greater than or equal to about 280° C. 
     
     
       17. An image sensor comprising the organic photoelectric device of  claim 9 . 
     
     
       18. The image sensor of  claim 17 , further comprising:
 a semiconductor substrate integrated with a plurality of first photo-sensing devices configured to sense light in a blue wavelength region and a plurality of second photo-sensing devices configured to sense light in a red wavelength region, 
 wherein the organic photoelectric device is on the semiconductor substrate and is configured to sense light in a green wavelength region. 
 
     
     
       19. The image sensor of  claim 18 , further comprising:
 a color filter layer between the semiconductor substrate and the organic photoelectric device, the color filter layer including a blue filter configured to selectively transmit light in the blue wavelength region and a red filter configured to selectively transmit light in the red wavelength region. 
 
     
     
       20. The image sensor of  claim 18 , wherein the first photo-sensing devices and the second photo-sensing devices are stacked in a vertical direction on the semiconductor substrate. 
     
     
       21. The image sensor of  claim 17 , wherein
 the organic photoelectric device is a green photoelectric device, and 
 the green photoelectric device, a blue photoelectric device configured to sense light in a blue wavelength region, and a red photoelectric device configured to sense light in a red wavelength region are stacked. 
 
     
     
       22. An electronic device comprising the image sensor of  claim 17 .